Organic polyhydroxy compound



Patented Jan. 27, 1948 ORGANIC POLYHYDROXY COMPOUND Joseph E. Bludworth, Corpus Christi, Tex., and Donald P. Easter, Washington, D. 0., assignors to Celanese Corporation of America, a corporation of Delaware No Drawing. Orig nal application September 19,

1944, Serial No. 554,858.

Divided and this application April 25, 1946, Serial No. 664,979

1 This invention relates to the novel organic compound 1-(3,4-dihydroxycyclohexyl) -1,2 dihydroxybutanone having the following formula on, on on no-cn cn-cn-tn-g-cm no-cn H. o

This application is a division of our application 5. No. 554,858, filed September 19, 1944.

An object of our invention is the preparation of l-(3,4-dihydroxycyclohexyl)-1,2 dihydroxybutanone.

Other objects of our invention will appear from the following detailed description.

In accordance with the Diels-Alder reaction, the condensation of acrolein with butadiene yields A -tetrahydrobenzaldehyde. On reacting this aldehyde with acetone in the presence of potassium hydroxide, p -(A tetrahydrophenyl) vinyl methyl ketone is formed,

CH: which yields many valuable compounds on further reaction.

We have now discovered that by effecting the oxidation of ,3 (A tetrahydrophenyl) vinyl methyl ketone, a novel higher molecular weight polyhydric alcohol may be obtained, namely, 1-

(3,4 dihydroxycyclohexyl) 1,2 dihydroxybu tanone.

As suitable oxidizing agents there may be mentioned potassium permanganate, hydrogen peroxide or sodium chlorate but the most desirable results are obtained employing potassium permanganate. The oxidation may be carried out at tem peratures of from to 15 C. When employing potassium permanganate as the oxidizing agent, the reaction is preferably allowed to proceed grad ually, employing from 80 to 90 parts by weight of a 1 to 7% aqueous solution of the potassium permanganate, the reactants being held at a temperature of 0 to 5 C. for 1 to 4 hours and then allowed to rise to room temperature. The reaction may be completed by heating at about 100 C. for 1 to 3 hours. The 1-(3,4-dihydroxycyclohexyl) 1,2-dihydroxybutanone formed may be separated from the reaction by extraction employing a suitable water-immiscible solvent such as diethyl ether.

In order further to illustrate our invention, but

5 Claims. (Cl. 260-586) without being limited thereto, the following example is given:

Example 30 parts by weight of (A -tetrahydrophenyh vinyl methyl ketone are suspended in 200 parts of water and cooled to 5 C. A solution of 63 parts by weight of potassium permanganate in 1000 parts of water is added over a period of one and onehalf hours while maintaining the temperature below 5 C. at all times. The mixture obtained is allowed to warm at room temperature, 1. e. about 20 C., and then heated on a steam bath for one hour. The precipitated manganese dioxide is filtered off, the filtrate saturated with sodium sulfate and then extracted with ether. The ether extract is dried over anhydrous sodium sulfate and is then evaporated to remove the ether. The residue comprises impure 1-(3,4-dihydroxycyclohexyl);1,2-dihydroxybutanone. The yield obtained is over 95% of theoretical. This compound is compatible with cellulose acetate and may be employed as a plasticizer therefor.

It is to be understood that the foregoing detailed description is given merely by way of i11ustration and that many variations may be made therein without departing from the spirit of our invention.

Having described our invention, What we de sire to secure by Letters Patent is:

1. As a new compound, l-(3,4-dihydroxycyc1ohexyl) -1,2-dihydroxybutanone having the following formula 2. Process for the production of 1-(3,4-dihydroxycyclohexyl)-1,2-dihydroxybutanone, which comprises subjecting ,B-(A tetrahydrophenyD- vinyl methyl ketone-to' the action of an aqueous solution of potassium permanganate.

3. Process for the-production of 1-(3,4-dihydroxycyclohexyl)-1,2-dihydroxybutanone, which comprises subjecting p-(A -tetrahydrophenyhvinyl methyl ketone to the action of a 1 to 7% aqueous solution of potassium permanganate.

4. Process for the'production of 1-(3,4-dihydroxycyclohexyl)-l,g,-dihydroxybutanone, which comprises subjecting-30 parts by weight of fi-(A tetrahydrophenyl) -vinyl methyl ketone to the action of 35 to parts iby weight of a 1 to 7% aqueous solution of potassium permanganate.

5. Process for the production of l-(3,4-dihydroxycyclohexyl)-1,2-dihydroxybutanone, which comprises subjecting 30 parts by weight or p-(A REFERENCES CITED tetrahydrophenyl) -viny1 methyl ketone to the acon of 35 to 90 parts by weight of a 1 to 7% aque The following references are of record in the ous solution of. potassium permanganate at a 5 m ofvthis Patent:

temperature ofLO to 15C. for 1-to14.11aurs;,raisingt the temperature to 60 to 100 C. for 1 to 3 hours, FOREIGN PATENTS and separating the 1-(3,4-dihydroxycyc1ohexy13 1,2-dihydroxybutanone formed. I v l g; g

JOSEPH E. BLUDWOR'IH. 10 y DONALD P, A TE 

